荧光类非离子表面活性剂的设计与合成

Design and Synthesis of Fluorescent Non-Ionic Surfactants

以萘酰亚胺为荧光母体、酰胺基团为连接基,将萘酰亚胺引入到典型的非离子表面活性剂脂肪醇聚氧乙烯醚中,设计并合成了两种荧光类非离子表面活性剂化合物(Ⅲa和Ⅲb),并用质谱、核磁共振光谱和傅里叶变换红外光谱对目标产物进行了结构表征,测量了化合物Ⅲa和Ⅲb的荧光及表面性能。实验结果表明,这两种化合物不仅具有传统表面活性剂的一般性质,而且还表现出良好的荧光性质。化合物Ⅲa和Ⅲb在水溶液中的荧光最大发射波长分别为540,543nm,激发波长均为452nm;临界胶束浓度分别为1.148×10-5,4.070×10-6m ol/L;最低表面张力分别为31.29,31.73mN/m;浊点分别为40.1,44.2℃。

Research of fluorescent compounds used as fluorescence probe in surfactant field are becoming important because they have sensitive fluorescent signals and can be conveniently detected. But their poor water-solubility usually limits their application. To improve water-solubility of the surfactant as a tracer used in oil recovery and obtain appropriate fluorescent probe, two fluorescent nonionic surfactants Ⅲa and Ⅲb were designed and synthesized from naphthalimide and polyoxyethylene dodecyl ether with amido link. They were characterized by means of MS, 1R, ^1H NMR and fluorescence spectrum. Ⅲa and Ⅲb not only showed same major features as other conventional surfactants but also exhibited good fluorescence properties. The strongest fluorescence emission wavelengths of Ⅲa and Ⅲb at excited wavelength 452 nm in aqueous solution were 540 and 543 nm, respectively. The critical micelle concentrations（CMC）of Ⅲa and Ⅲb were 1. 148 × 10^-5 mol/L and 4.070 × 10^-6 mol/L, respectively. Their surface tensions at CMC were 31.29 mN/m and 31.73 mN/m, respectively. Their cloud points were 40. 1℃ and 44.2℃, respectively. The experimental results showed that aim of molecular design had been fulfilled.